BFF to BF? 4 Factors to Consider Before Dating Your Best Friend

Yesterday, I was talking about how awesome it was to have Jake Stein* along on the weekend trip--and also talking about how Jake and I went from being best friends to being boyfriend-and-girlfriend for a brief period.

The question of our dating came up like this: Jake and I had gone back to his apartment for a nightcap after having dinner together ... and suddenly, he leaned over to kiss me.

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"What are you doing?" I said, thinking he was just feeling randy, and annoyed that he would risk our friendship on a whim.

But he told me he'd been mulling it over for a while, and he was serious about wanting to give things a go.

I hesitated. I really loved Jake. I respected him. I had a great time with him--we were always laughing; always talking about interesting things; always comfortable discussing our emotions, fears and insecurities. (Or, at least, MY insecurities.) His writing career was going well, and the work he did interested me. He had an amazingly awesome family. He was generous and kind. We liked the same kind of music and movies. Plus, he's very tall and quite handsome--an indubitably attractive guy (whom the ladies generally love). In other words, it was hard to imagine a more ideal boyfriend.

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Yet ... for whatever decidedly peculiar reason, I'd never felt an overwhelming urge to get it on with him.

What's more, I was terrified we might ruin the friendship. And not having Jake in my life seemed unimaginably painful.

At the same time, after considering it for a minute or two, I realized that if I didn't give it a try, my reluctance could create a weird dynamic which could very well do serious damage to the friendship--maybe as much as a failed romance would.

I also wondered if my hesitation had to do with a (lingering?) case of commitment-phobia on my part, rather than any real doubts about the situation at hand; maybe the supposed chemistry conundrum was just a cover for my fear of getting closer to him. And so I decided that the very best thing I could do was to give it a shot and see what happened--in part because I also felt fairly confident, upon reflection, that my friendship with Jake was strong enough to survive just about anything.

So we tried. We dated. And it wasn't terrible ... but it wasn't very good either. We still laughed a lot, but less. We seemed to have less to talk about, too. And I really do think, after all, that the main problem was our lack of chemistry. Maybe incompatible phermones are to blame--who knows?--because there doesn't seem to be much else to explain it. Yet, the lack of sexual heat was an indisputable fact. (Trust me on that: About six months after we broke up, Jake said, "The sex really wasn't very good, was it?" And indeed, it was not.)

Still, the break-up--understandable and inevitable though it was--hurt. And it had me convinced I would never find love. After all, if I couldn't make it work with this person I cared so deeply about, and got along so well with, how in the hell was I ever going to make anything work?

It took a few months before Jake and I began to hang out again. But then one afternoon, after we'd both (independently) moved out of D.C. to return to New York, I was getting my hair cut at my old favorite place--Antonio Prieto--when it dawned on me that I was just down the street from Jake's new office. (We had always been in tentative e-mail, even after the split.) I texted Jake, told him I was nearby, that I'd get out of the salon around 630--and did he want to grab a drink at that point?

He did ... and luckily, after that, our friendship fell back into place fairly quickly. And thank Buddha for that, because, have I mentioned I adore this person? (Dear me, I'm even tearing up a little as I write this.)

Anyway, the experience has me convinced that BOTH friends need to feel pretty strong chemistry before they move from being platonic pals to romantic partners. Otherwise, I think the chance of it working out are slim.

Which brings me to my thought about ...

THE FACTORS THAT SHOULD BE IN PLAY BEFORE YOU START DATING YOUR BEST FRIEND

1) A mutual (and intense) desire--ON BOTH SIDES--to give it a whirl.

2) The LACK of some major precipitating event. By that, I mean: Think twice before getting involved with your best friend if either of you are motivated by feelings other than love, longing and desire. If, instead, the catalyst seems to be a tragedy (like a death in the family) or even a great personal victory (like a big promotion or selling your first movie script), you might want to hold off a month or two, and re-assess then. Sometimes major life events can cloud our judgement, and make us so depressed--or euphoric--that we make bad decisions. Similarly, don't start dating your best friend if you've just been brutally dumped by someone and you're feeling bad about yourself--or if your friend has just had a similar experience. (If he's just broken up with someone after realizing how much he cares about you, that's a different story!)

3) General emotional stability on both sides. If you suspect your friend might have a drinking problem, or you think you are struggling with an anxiety problem or other psychological disorder, I'd hold off temporarily on changing the boundaries of your relationship. Make sure whomever needs the help gets some treatment, and then let the dust settle for a month or two. If, after that, your feelings are as strong as ever, take the risk.

What do you think, guys? Does all this sound on target to you? Did you ever start dating your best friend as you were helping him through the worst--or most exciting--transition in his life? And did it lead to love or loss?

xxx

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*Not his real name.

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PS: Staci: I love your story! How awesome for you. I'm glad it worked out--good for you, for being bold enough to lay it on the line! ... Faith, I'm sorry things didn't work out with your friend, but it sounds like you have a great outlook on it. And I think failed relationships really can teach us many valuable lessons that make it easier to make subsequent ones work. Hang in there! (Also, don't forget that even Harry and Sally broke up once before they finally got back together forever!)